| 1 | Sat 11 Oct | 71-5 v Grantham TownGrantham Town 5-1 Winterton Rangers | Lincolnshire Senior Trophy First Round |
| 2 | Wed 15 Oct | 141-9 v Route One RoversRoute One Rovers 9-1 Winterton Rangers | Northern Counties East League Division One |
| 3 | Sat 18 Oct | 172-1 v Glasshoughton WelfareWinterton Rangers 2-1 Glasshoughton Welfare | Northern Counties East League Division One |
| 4 | Wed 22 Oct | 71-1 v Ilkley TownWinterton Rangers 1-1 Ilkley Town | Northern Counties East League Division One |
| 5 | Sat 25 Oct | 71-4 v Harrogate Railway AthleticHarrogate Railway Athletic 4-1 Winterton Rangers | Northern Counties East League Division One |
| 6 | Sat 1 Nov | 110-3 v Dearne & DistrictWinterton Rangers 0-3 Dearne & District | Northern Counties East League Division One |
| 7 | Sat 8 Nov | 110-2 v Louth TownLouth Town 2-0 Winterton Rangers | Northern Counties East League Division One |
| 8 | Sat 22 Nov | 113-0 v Nostell Miners WelfareWinterton Rangers 3-0 Nostell Miners Welfare | Northern Counties East League Division One |
| 9 | Wed 26 Nov | 121-6 v Route One RoversWinterton Rangers 1-6 Route One Rovers | Northern Counties East League Cup Third Round |
| 10 | Sat 6 Dec | 113-0 v Athersley RecreationAthersley Recreation 0-3 Winterton Rangers | Northern Counties East League Division One |
| 11 | Sat 13 Dec | 72-4 v Club Thorne CollieryWinterton Rangers 2-4 Club Thorne Colliery | Northern Counties East League Division One |
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